Affiliation:
1. Research Institute of Pulp & Paper Engineering, Hubei University of Technology, Wuhan 430068, China
2. Hubei Provincial Key Laboratory of Green Materials for Light Industry, Hubei University of Technology, Wuhan 430068, China
Abstract
In this paper, guaiacyl dehydrogenated lignin polymer (G-DHP) was synthesized using coniferin as a substrate in the presence of β-glucosidase and laccase. Carbon-13 nuclear magnetic resonance (13C-NMR) determination revealed that the structure of G-DHP was relatively similar to that of ginkgo milled wood lignin (MWL), with both containing β-O-4, β-5, β-1, β-β, and 5-5 substructures. G-DHP fractions with different molecular weights were obtained by classification with different polar solvents. The bioactivity assay indicated that the ether-soluble fraction (DC2) showed the strongest inhibition of A549 lung cancer cells, with an IC50 of 181.46 ± 28.01 μg/mL. The DC2 fraction was further purified using medium-pressure liquid chromatography. Anti-cancer analysis revealed that the D4 and D5 compounds from DC2 had better anti-tumor activity, with IC50 values of 61.54 ± 17.10 μg/mL and 28.61 ± 8.52 μg/mL, respectively. Heating electrospray ionization tandem mass spectrometry (HESI-MS) results showed that both the D4 and D5 were β-5-linked dimers of coniferyl aldehyde, and the 13C-NMR and 1H-NMR analyses confirmed the structure of the D5. Together, these results indicate that the presence of an aldehyde group on the side chain of the phenylpropane unit of G-DHP enhances its anticancer activity.
Funder
National Natural Science Foundation of China
Outstanding Young and Middle-aged Technological Innovation Team Project of Hubei Provincial Universities
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science